In this episode, Darius Houle joins the conversation to explore the real-world limitations of AI in problem-solving and why context matters more than most people realize. The discussion covers how AI systems struggle with nuanced tasks, why developers must understand the boundaries of these tools, and how clearer prompts can dramatically improve outcomes.

Darius shares insights from his experience in application security, tool building, and community leadership. The conversation also highlights the growing role of AI in cybersecurity testing and the responsibility developers have when integrating AI into their workflows.

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Connect with Darius Houle

LinkedIn: https://www.linkedin.com/in/dariushoule/

Trail of Bits Skills Marketplace: https://github.com/trailofbits/skills

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

X: https://x.com/PhillipWylie

Instagram: https://www.instagram.com/phillipwylie

00:00 Introduction to Darius Houle and Trillobits
03:18 Darius Houle’s Origin Story in Cybersecurity
05:41 The Importance of Foundational Knowledge in AppSec
08:33 The Role of AI in Cybersecurity
10:52 AI Tools and Their Impact on Security Testing
13:36 Getting Started with AI in Cybersecurity
16:30 Building Tools in the Security Community
18:55 Darius’s Recent Talk at DistrictCon
21:25 Vulnerabilities in the Electron Framework
23:57 Highlights from DistrictCon
26:28 Conclusion and Resources
28:54 Simply Offensive Outro